4-Amino-2-hy-droxy-benzohydrazide.

The asymmetric unit of the title compound, C(7)H(9)N(3)O(2), comprises two crystallographically independent mol-ecules (A and B). In each mol-ecule there is an intra-molecular O-H⋯O hydrogen bond making an S(6) ring motif. In the crystal, a pair of N-H⋯N hydrogen bonds link the two mol-ecules (A and B) into a dimer with an R(2) (2)(6) ring motif. The B mol-ecules are linked via pairs of N-H⋯O hydrogen bonds, forming inversion dimers with an R(2) (2)(10) ring motif. The mol-ecules are further linked via other N-H⋯O hydrogen bonds, forming undulating two-dimensional networks lying parallel to the bc plane. These networks are finally linked via N-H⋯O hydrogen bonds, forming a three-dimensional structure.

Related literature

For background to Schiff bases derived from benzohydrazide, see: Xu (2012 ▶); Bakir & Green (2002 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H9N3O2

M = 167.17

Monoclinic,

a = 5.6424 (3) Å

b = 18.3221 (12) Å

c = 14.7164 (9) Å

β = 94.087 (3)°

V = 1517.52 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 291 K

0.32 × 0.16 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.965, T max = 0.985

12530 measured reflections

3366 independent reflections

2092 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.133

S = 1.01

3366 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶)’; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026190/su2448sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026190/su2448Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026190/su2448Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H9N3O2	F(000) = 704
Mr = 167.17	Dx = 1.463 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2540 reflections
a = 5.6424 (3) Å	θ = 2.5–27.4°
b = 18.3221 (12) Å	µ = 0.11 mm−1
c = 14.7164 (9) Å	T = 291 K
β = 94.087 (3)°	Needle, colourless
V = 1517.52 (16) Å3	0.32 × 0.16 × 0.14 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	3366 independent reflections
Radiation source: fine-focus sealed tube	2092 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 27.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.965, Tmax = 0.985	k = −23→23
12530 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0609P)2 + 0.2376P] where P = (Fo2 + 2Fc2)/3
3366 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.1395 (3)	0.65395 (10)	0.73974 (11)	0.0391 (4)
C2	0.2934 (3)	0.68029 (9)	0.81762 (11)	0.0364 (4)
C3	0.4957 (3)	0.72159 (9)	0.80167 (11)	0.0369 (4)
C4	0.6503 (3)	0.74457 (10)	0.87301 (11)	0.0398 (4)
H4	0.7847	0.7712	0.8608	0.048*
C5	0.6085 (3)	0.72868 (9)	0.96218 (11)	0.0386 (4)
C6	0.4041 (3)	0.68873 (10)	0.97971 (11)	0.0430 (4)
H6	0.3718	0.6781	1.0394	0.052*
C7	0.2524 (3)	0.66546 (10)	0.90872 (11)	0.0414 (4)
H7	0.1179	0.6390	0.9213	0.050*
C8	0.3586 (3)	0.46432 (10)	0.83167 (11)	0.0411 (4)
C9	0.2091 (3)	0.44085 (9)	0.75099 (11)	0.0363 (4)
C10	0.0013 (3)	0.40061 (10)	0.76272 (11)	0.0402 (4)
C11	−0.1501 (3)	0.38160 (10)	0.68907 (12)	0.0442 (5)
H11	−0.2893	0.3564	0.6985	0.053*
C12	−0.0989 (3)	0.39927 (10)	0.60123 (12)	0.0428 (4)
C13	0.1119 (3)	0.43658 (10)	0.58807 (11)	0.0415 (4)
H13	0.1520	0.4475	0.5294	0.050*
C14	0.2596 (3)	0.45715 (10)	0.66168 (11)	0.0405 (4)
H14	0.3978	0.4827	0.6518	0.049*
N1	0.7591 (3)	0.75402 (10)	1.03293 (10)	0.0567 (5)
H1A	0.8806	0.7800	1.0218	0.068*
H1B	0.7317	0.7438	1.0883	0.068*
N2	−0.0459 (3)	0.61215 (8)	0.75474 (10)	0.0445 (4)
H2	−0.0935	0.5975	0.8151	0.053*
N3	−0.2002 (3)	0.58528 (9)	0.68260 (10)	0.0486 (4)
H1N3	−0.1141	0.5589	0.6368	0.058*
H2N3	−0.2503	0.6231	0.6408	0.058*
N4	−0.2532 (3)	0.38142 (11)	0.52828 (11)	0.0686 (6)
H4A	−0.3835	0.3590	0.5369	0.082*
H4B	−0.2195	0.3927	0.4740	0.082*
N5	0.5410 (3)	0.50862 (9)	0.81992 (9)	0.0468 (4)
H5	0.5880	0.5239	0.7595	0.056*
N6	0.6986 (3)	0.53248 (10)	0.89273 (9)	0.0519 (4)
H1N6	0.6126	0.5492	0.9381	0.062*
H2N6	0.7604	0.4892	0.9220	0.062*
O1	0.5463 (2)	0.74076 (8)	0.71656 (8)	0.0523 (4)
H1	0.4410	0.7260	0.6799	0.078*
O2	0.1813 (2)	0.66956 (8)	0.65963 (8)	0.0560 (4)
O3	−0.0582 (2)	0.37996 (8)	0.84652 (8)	0.0566 (4)
H3	0.0483	0.3916	0.8846	0.085*
O4	0.3139 (3)	0.44440 (8)	0.90981 (8)	0.0619 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0420 (10)	0.0386 (10)	0.0370 (10)	0.0033 (8)	0.0057 (8)	−0.0009 (8)
C2	0.0371 (9)	0.0374 (10)	0.0347 (9)	0.0031 (8)	0.0033 (7)	−0.0009 (7)
C3	0.0398 (10)	0.0382 (10)	0.0335 (9)	0.0054 (8)	0.0086 (7)	0.0005 (7)
C4	0.0356 (9)	0.0423 (10)	0.0420 (10)	−0.0012 (8)	0.0076 (8)	−0.0012 (8)
C5	0.0393 (10)	0.0406 (10)	0.0358 (9)	0.0065 (8)	0.0012 (7)	−0.0061 (8)
C6	0.0486 (11)	0.0490 (11)	0.0319 (9)	0.0020 (9)	0.0069 (8)	0.0009 (8)
C7	0.0402 (10)	0.0440 (10)	0.0409 (10)	−0.0023 (8)	0.0085 (8)	0.0026 (8)
C8	0.0438 (10)	0.0449 (11)	0.0349 (9)	0.0046 (9)	0.0038 (8)	0.0002 (8)
C9	0.0392 (9)	0.0370 (10)	0.0328 (9)	0.0022 (8)	0.0043 (7)	0.0016 (7)
C10	0.0474 (10)	0.0355 (10)	0.0389 (10)	0.0015 (8)	0.0111 (8)	0.0040 (8)
C11	0.0444 (11)	0.0407 (11)	0.0485 (11)	−0.0104 (8)	0.0091 (9)	−0.0032 (8)
C12	0.0458 (11)	0.0386 (10)	0.0437 (10)	−0.0017 (9)	0.0018 (8)	−0.0082 (8)
C13	0.0454 (10)	0.0464 (11)	0.0333 (9)	−0.0019 (9)	0.0068 (8)	0.0013 (8)
C14	0.0385 (10)	0.0448 (10)	0.0383 (10)	−0.0038 (8)	0.0040 (8)	0.0028 (8)
N1	0.0553 (10)	0.0755 (12)	0.0390 (9)	−0.0105 (9)	0.0000 (7)	−0.0084 (8)
N2	0.0430 (9)	0.0514 (10)	0.0387 (8)	−0.0073 (7)	0.0012 (7)	−0.0050 (7)
N3	0.0503 (9)	0.0544 (10)	0.0401 (8)	−0.0057 (8)	−0.0036 (7)	−0.0062 (7)
N4	0.0645 (11)	0.0898 (14)	0.0508 (10)	−0.0334 (10)	0.0001 (9)	−0.0121 (9)
N5	0.0470 (9)	0.0578 (10)	0.0352 (8)	−0.0085 (8)	−0.0004 (7)	−0.0034 (7)
N6	0.0514 (9)	0.0648 (11)	0.0386 (8)	−0.0061 (8)	−0.0030 (7)	−0.0081 (7)
O1	0.0553 (9)	0.0687 (9)	0.0332 (7)	−0.0120 (7)	0.0064 (6)	0.0044 (6)
O2	0.0613 (9)	0.0737 (10)	0.0329 (7)	−0.0143 (7)	0.0018 (6)	0.0007 (6)
O3	0.0632 (9)	0.0657 (9)	0.0424 (7)	−0.0113 (8)	0.0128 (6)	0.0108 (7)
O4	0.0692 (10)	0.0838 (11)	0.0324 (7)	−0.0133 (8)	0.0014 (6)	0.0080 (7)

C1—O2	1.252 (2)	C11—C12	1.383 (2)
C1—N2	1.328 (2)	C11—H11	0.9300
C1—C2	1.469 (2)	C12—N4	1.373 (2)
C2—C7	1.403 (2)	C12—C13	1.397 (2)
C2—C3	1.403 (2)	C13—C14	1.372 (2)
C3—O1	1.3506 (19)	C13—H13	0.9300
C3—C4	1.382 (2)	C14—H14	0.9300
C4—C5	1.381 (2)	N1—H1A	0.8600
C4—H4	0.9300	N1—H1B	0.8600
C5—N1	1.377 (2)	N2—N3	1.4125 (19)
C5—C6	1.406 (2)	N2—H2	0.9837
C6—C7	1.371 (2)	N3—H1N3	0.9851
C6—H6	0.9300	N3—H2N3	0.9568
C7—H7	0.9300	N4—H4A	0.8600
C8—O4	1.249 (2)	N4—H4B	0.8600
C8—N5	1.331 (2)	N5—N6	1.4123 (19)
C8—C9	1.471 (2)	N5—H5	0.9858
C9—C14	1.397 (2)	N6—H1N6	0.9064
C9—C10	1.406 (2)	N6—H2N6	0.9561
C10—O3	1.355 (2)	O1—H1	0.8200
C10—C11	1.376 (2)	O3—H3	0.8200
O2—C1—N2	119.45 (16)	C10—C11—H11	119.4
O2—C1—C2	121.28 (16)	C12—C11—H11	119.4
N2—C1—C2	119.26 (15)	N4—C12—C11	120.81 (17)
C7—C2—C3	117.12 (15)	N4—C12—C13	120.45 (17)
C7—C2—C1	123.58 (16)	C11—C12—C13	118.74 (16)
C3—C2—C1	119.29 (15)	C14—C13—C12	120.03 (16)
O1—C3—C4	117.51 (16)	C14—C13—H13	120.0
O1—C3—C2	121.56 (15)	C12—C13—H13	120.0
C4—C3—C2	120.93 (15)	C13—C14—C9	122.08 (17)
C5—C4—C3	121.11 (17)	C13—C14—H14	119.0
C5—C4—H4	119.4	C9—C14—H14	119.0
C3—C4—H4	119.4	C5—N1—H1A	120.0
N1—C5—C4	120.65 (17)	C5—N1—H1B	120.0
N1—C5—C6	120.48 (16)	H1A—N1—H1B	120.0
C4—C5—C6	118.83 (15)	C1—N2—N3	121.79 (14)
C7—C6—C5	119.88 (16)	C1—N2—H2	125.2
C7—C6—H6	120.1	N3—N2—H2	113.0
C5—C6—H6	120.1	N2—N3—H1N3	112.2
C6—C7—C2	122.10 (17)	N2—N3—H2N3	111.6
C6—C7—H7	118.9	H1N3—N3—H2N3	93.0
C2—C7—H7	118.9	C12—N4—H4A	120.0
O4—C8—N5	120.42 (16)	C12—N4—H4B	120.0
O4—C8—C9	121.05 (17)	H4A—N4—H4B	120.0
N5—C8—C9	118.51 (15)	C8—N5—N6	122.74 (15)
C14—C9—C10	117.09 (15)	C8—N5—H5	123.3
C14—C9—C8	123.60 (16)	N6—N5—H5	113.7
C10—C9—C8	119.31 (15)	N5—N6—H1N6	108.8
O3—C10—C11	117.79 (16)	N5—N6—H2N6	105.9
O3—C10—C9	121.39 (16)	H1N6—N6—H2N6	98.4
C11—C10—C9	120.82 (15)	C3—O1—H1	109.5
C10—C11—C12	121.17 (17)	C10—O3—H3	109.5
O2—C1—C2—C7	178.86 (16)	O4—C8—C9—C10	5.5 (3)
N2—C1—C2—C7	−1.8 (3)	N5—C8—C9—C10	−173.19 (15)
O2—C1—C2—C3	−2.3 (3)	C14—C9—C10—O3	177.62 (16)
N2—C1—C2—C3	177.02 (16)	C8—C9—C10—O3	−3.2 (3)
C7—C2—C3—O1	−177.79 (15)	C14—C9—C10—C11	−3.1 (3)
C1—C2—C3—O1	3.3 (2)	C8—C9—C10—C11	176.03 (16)
C7—C2—C3—C4	1.8 (2)	O3—C10—C11—C12	−178.52 (16)
C1—C2—C3—C4	−177.12 (16)	C9—C10—C11—C12	2.2 (3)
O1—C3—C4—C5	178.53 (16)	C10—C11—C12—N4	−178.66 (17)
C2—C3—C4—C5	−1.1 (3)	C10—C11—C12—C13	0.5 (3)
C3—C4—C5—N1	−177.69 (16)	N4—C12—C13—C14	177.00 (17)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—C14	−2.2 (3)
N1—C5—C6—C7	178.29 (16)	C12—C13—C14—C9	1.2 (3)
C4—C5—C6—C7	0.9 (3)	C10—C9—C14—C13	1.4 (3)
C5—C6—C7—C2	−0.1 (3)	C8—C9—C14—C13	−177.66 (16)
C3—C2—C7—C6	−1.2 (3)	O2—C1—N2—N3	−0.7 (3)
C1—C2—C7—C6	177.67 (16)	C2—C1—N2—N3	179.94 (15)
O4—C8—C9—C14	−175.39 (17)	O4—C8—N5—N6	3.1 (3)
N5—C8—C9—C14	5.9 (3)	C9—C8—N5—N6	−178.16 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.80	2.5297 (18)	147
O3—H3···O4	0.82	1.80	2.528 (2)	147
N2—H2···N6i	0.98	2.07	2.958 (2)	149
N5—H5···N3ii	0.99	2.04	2.934 (2)	150
N6—H1N6···O4iii	0.91	2.25	2.9424 (18)	133
N1—H1B···O1iv	0.86	2.24	3.0358 (19)	154
N4—H4B···O2v	0.86	2.30	2.974 (2)	136
N6—H2N6···O3ii	0.96	2.54	3.207 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.80	2.5297 (18)	147
O3—H3⋯O4	0.82	1.80	2.528 (2)	147
N2—H2⋯N6i	0.98	2.07	2.958 (2)	149
N5—H5⋯N3ii	0.99	2.04	2.934 (2)	150
N6—H1N6⋯O4iii	0.91	2.25	2.9424 (18)	133
N1—H1B⋯O1iv	0.86	2.24	3.0358 (19)	154
N4—H4B⋯O2v	0.86	2.30	2.974 (2)	136
N6—H2N6⋯O3ii	0.96	2.54	3.207 (2)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .